DFT Calculations and ROESY NMR Data for the Diastereochemical Characterization of Cytotoxic Tetraterpenoids from the Oleoresin of Abies balsamea

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• 作者：Serge Lavoie ; Charles Gauthier ; Vakhtang Mshvildadze ; Jean Legault ; Benoit Roger ; André Pichette
• 刊名：Journal of Natural Products
• 出版年：2015
• 出版时间：December 24, 2015
• 年：2015
• 卷：78
• 期：12
• 页码：2896-2907
• 全文大小：630K
• ISSN：1520-6025

文摘

Eight non-carotenoid tetraterpenoids, abibalsamins C–J (3–10), were isolated from the oleoresin of Abies balsamea. Their chemical structures were determined based on analysis of 1D/2D NMR and MS data. The assignment of their relative configurations was accomplished using homonuclear coupling constants in tandem with ROESY data. However, the presence of two stereogenic centers on a flexible side chain complicated the characterization. In silico models and ROESY data were analyzed in order to assign relative configurations of the isolated tetraterpenoids. Abibalsamins B and H–J showed moderate cytotoxicity against human A549 lung carcinoma cells, with IC₅₀ values ranging between 6.7 and 10 μM.